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Volumn 1, Issue 8, 2013, Pages 929-936

Aqueous extract of Acacia concinna pods: An efficient surfactant type catalyst for synthesis of 3-carboxycoumarins and cinnamic acids via knoevenagel condensation

Author keywords

3 Carboxycoumarins; Acacia concinna; Cinnamic acids; Green protocol; Knoevenagel condensation; Surfactant

Indexed keywords

3-CARBOXYCOUMARINS; ACACIA CONCINNA; AQUEOUS EXTRACTS; CINNAMIC ACIDS; ENVIRONMENTALLY BENIGN; KNOEVENAGEL CONDENSATION; LARGE SCALE PREPARATION; NATURALLY OCCURRING;

EID: 84881415735     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc4000237     Document Type: Article
Times cited : (57)

References (55)
  • 1
    • 0004098009 scopus 로고
    • Tramper, J. Vander Plas, H. Linko, P. Elsevier: Amsterdam
    • Alfermann, A. Biocatalysis in Organic Synthesis; Tramper, J., Vander Plas, H., Linko, P., Eds.; Elsevier: Amsterdam, 1985, p 25.
    • (1985) Biocatalysis in Organic Synthesis , pp. 25
    • Alfermann, A.1
  • 2
    • 0034736426 scopus 로고    scopus 로고
    • Preparative synthesis of chiral alcohols by enantioselective reduction with Daucus carota root as biocatalyst
    • Baladassare, F.; Bertoni, G.; Chiappe, C.; Marioni, F. Preparative synthesis of chiral alcohols by enantioselective reduction with Daucus carota root as biocatalyst J. Mol. Catal. B: Enzym. 2000, 11, 55-58
    • (2000) J. Mol. Catal. B: Enzym. , vol.11 , pp. 55-58
    • Baladassare, F.1    Bertoni, G.2    Chiappe, C.3    Marioni, F.4
  • 3
    • 0035843122 scopus 로고    scopus 로고
    • Enzymes for chemical synthesis
    • Koeller, K. M.; Wong, C. H. Enzymes for chemical synthesis Nature 2001, 409, 232-240
    • (2001) Nature , vol.409 , pp. 232-240
    • Koeller, K.M.1    Wong, C.H.2
  • 4
    • 0001512380 scopus 로고
    • Biotransformation of acetoacetic ester with immobilized cells of nicotiana tabacum
    • Naoshima, Y.; Akakabe, Y.; Watanabe, F. Biotransformation of acetoacetic ester with immobilized cells of nicotiana tabacum Agric. Biol. Chem. 1989, 53, 545-547
    • (1989) Agric. Biol. Chem. , vol.53 , pp. 545-547
    • Naoshima, Y.1    Akakabe, Y.2    Watanabe, F.3
  • 5
    • 0000060265 scopus 로고
    • Biotransformation of some keto esters through the consecutive reuse of immobilized Nicotiana tabacum cells
    • Naoshima, Y.; Akakabe, Y. Biotransformation of some keto esters through the consecutive reuse of immobilized Nicotiana tabacum cells J. Org. Chem. 1989, 54, 4237-4239
    • (1989) J. Org. Chem. , vol.54 , pp. 4237-4239
    • Naoshima, Y.1    Akakabe, Y.2
  • 6
    • 0000972375 scopus 로고
    • Biotransformation of aromatic ketones with cell cultures of carrot, tobacco and Gardenia
    • Naoshima, Y.; Akakabe, Y. Biotransformation of aromatic ketones with cell cultures of carrot, tobacco and Gardenia Phytochemistry 1991, 30, 3595-3597
    • (1991) Phytochemistry , vol.30 , pp. 3595-3597
    • Naoshima, Y.1    Akakabe, Y.2
  • 7
    • 0037204732 scopus 로고    scopus 로고
    • Efficient enantioselective reduction of ketones with Daucus carota root
    • Yadav, J. S.; Nanda, S.; Reddy, P. T.; Rao, A. B. Efficient enantioselective reduction of ketones with Daucus carota root J. Org. Chem. 2002, 67, 3900-3903
    • (2002) J. Org. Chem. , vol.67 , pp. 3900-3903
    • Yadav, J.S.1    Nanda, S.2    Reddy, P.T.3    Rao, A.B.4
  • 8
    • 0033944031 scopus 로고    scopus 로고
    • Efficient synthesis of optically active 2-azido-1-arylethanols via oxazaborolidine-catalysed asymmetric borane reduction
    • Yadav, J. S.; Reddy, P. T.; Hashim, S. R. Efficient synthesis of optically active 2-azido-1-arylethanols via oxazaborolidine-catalysed asymmetric borane reduction Synlett 2000, 7, 1049-1051
    • (2000) Synlett , vol.7 , pp. 1049-1051
    • Yadav, J.S.1    Reddy, P.T.2    Hashim, S.R.3
  • 9
    • 0029969977 scopus 로고    scopus 로고
    • Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures
    • Chadha, A.; Manohar, M.; Soundararajan, T.; Lokeswari, T. S. Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures Tetrahedron: Asymmetry 1996, 7, 1571-1572
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1571-1572
    • Chadha, A.1    Manohar, M.2    Soundararajan, T.3    Lokeswari, T.S.4
  • 10
    • 0347355224 scopus 로고    scopus 로고
    • Highly stereoselective reduction of 4-aryl-2-oxo but-3-enoic carboxylic esters by plant cell culture of Daucus carota
    • Bhaskar, B.; Ganesh, S.; Lokeswari, T. S.; Chadha, A. Highly stereoselective reduction of 4-aryl-2-oxo but-3-enoic carboxylic esters by plant cell culture of Daucus carota J. Mol. Catal. B: Enzym. 2004, 27, 13-17
    • (2004) J. Mol. Catal. B: Enzym. , vol.27 , pp. 13-17
    • Bhaskar, B.1    Ganesh, S.2    Lokeswari, T.S.3    Chadha, A.4
  • 11
    • 0038539459 scopus 로고    scopus 로고
    • Soaked Phaseolus aureus L: An efficient biocatalyst for asymmetric reduction of prochiral aromatic ketones
    • Kumarswamy, G.; Ramesh, S. Soaked Phaseolus aureus L: An efficient biocatalyst for asymmetric reduction of prochiral aromatic ketones Green Chem. 2003, 5, 306-308
    • (2003) Green Chem. , vol.5 , pp. 306-308
    • Kumarswamy, G.1    Ramesh, S.2
  • 18
    • 50249237889 scopus 로고    scopus 로고
    • Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues
    • Zhoua, X.; Wanga, X.-B.; Wang, T.; Kong, L.-Y. Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues Bioorg. Med. Chem. 2008, 16, 8011-8021
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 8011-8021
    • Zhoua, X.1    Wanga, X.-B.2    Wang, T.3    Kong, L.-Y.4
  • 19
    • 0037179550 scopus 로고    scopus 로고
    • Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin
    • Wang, C. J.; Hsieh, Y. J.; Chu, C. Y.; Lin, Y. L.; Tseng, T. H. Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin Cancer Lett. 2002, 183, 163-168
    • (2002) Cancer Lett. , vol.183 , pp. 163-168
    • Wang, C.J.1    Hsieh, Y.J.2    Chu, C.Y.3    Lin, Y.L.4    Tseng, T.H.5
  • 23
    • 0001075710 scopus 로고
    • Synthesis and chemistry of 7-amino-4-(trifluoromethyl)coumarin and its amino acid and peptide derivatives
    • Bissel, E. R.; Mitchell, A. R.; Smith, R. E. Synthesis and chemistry of 7-amino-4-(trifluoromethyl)coumarin and its amino acid and peptide derivatives J. Org. Chem. 1980, 45, 2283-2287
    • (1980) J. Org. Chem. , vol.45 , pp. 2283-2287
    • Bissel, E.R.1    Mitchell, A.R.2    Smith, R.E.3
  • 24
    • 0033618260 scopus 로고    scopus 로고
    • Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents of α,β-unsaturated nitroacetates: An enantioselective route to β-arylnitroalkanes
    • Versleiien, L. P. G.; Van Leusen, A. M.; Feringa, B. L. Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents of α,β-unsaturated nitroacetates: An enantioselective route to β-arylnitroalkanes Tetrahedron Lett. 1999, 40, 5803-5806
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5803-5806
    • Versleiien, L.P.G.1    Van Leusen, A.M.2    Feringa, B.L.3
  • 25
    • 79958288624 scopus 로고    scopus 로고
    • Nickel nanoparticles catalyzed chemoselective Knoevenagel condensation of Meldrum's acid and tandem enol lactonizations via cascade cyclization sequence
    • Khurana, J. M.; Vij, K. Nickel nanoparticles catalyzed chemoselective Knoevenagel condensation of Meldrum's acid and tandem enol lactonizations via cascade cyclization sequence Tetrahedron Lett. 2011, 52, 3666-3669
    • (2011) Tetrahedron Lett. , vol.52 , pp. 3666-3669
    • Khurana, J.M.1    Vij, K.2
  • 26
    • 0037463416 scopus 로고    scopus 로고
    • A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho -hydroxyaryl aldehydes or ketones
    • Song, A.; Wang, X.; Lam, K. S. A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho -hydroxyaryl aldehydes or ketones Tetrahedron Lett. 2003, 44, 1755-1758
    • (2003) Tetrahedron Lett. , vol.44 , pp. 1755-1758
    • Song, A.1    Wang, X.2    Lam, K.S.3
  • 27
    • 0041331461 scopus 로고    scopus 로고
    • A practical and environmentally friendly preparation of 3-carboxycoumarins
    • Deshmukh, M. N.; Burud, R.; Baldino, C.; Chan, P. C. M.; Liu, J. A practical and environmentally friendly preparation of 3-carboxycoumarins Synth. Commun. 2003, 33, 3299-3303
    • (2003) Synth. Commun. , vol.33 , pp. 3299-3303
    • Deshmukh, M.N.1    Burud, R.2    Baldino, C.3    Chan, P.C.M.4    Liu, J.5
  • 28
    • 0033525186 scopus 로고    scopus 로고
    • Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids
    • Franca, B.; Luca, C.; Raimondo, M.; Giovanni, S. Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the Knoevenagel synthesis of coumarin-3-carboxylic acids J. Org. Chem. 1999, 64, 1033-1035
    • (1999) J. Org. Chem. , vol.64 , pp. 1033-1035
    • Franca, B.1    Luca, C.2    Raimondo, M.3    Giovanni, S.4
  • 29
    • 0242656278 scopus 로고    scopus 로고
    • One-pot synthesis of 3-carboxycoumarins via consecutive Knoevenagel and Pinner reactions in water
    • Fringuelli, F.; Piermatti, O.; Pizzo, F. One-pot synthesis of 3-carboxycoumarins via consecutive Knoevenagel and Pinner reactions in water Synthesis 2003, 15, 2331-2334
    • (2003) Synthesis , vol.15 , pp. 2331-2334
    • Fringuelli, F.1    Piermatti, O.2    Pizzo, F.3
  • 30
    • 79955550633 scopus 로고    scopus 로고
    • A novel light induced Knoevenagel condensation of Meldrum's acid with aromatic aldehydes in aqueous ethanol
    • Ghosh, S.; Das, J.; Chattopadhyay, S. A novel light induced Knoevenagel condensation of Meldrum's acid with aromatic aldehydes in aqueous ethanol Tetrahedron Lett. 2011, 52, 2869-2872
    • (2011) Tetrahedron Lett. , vol.52 , pp. 2869-2872
    • Ghosh, S.1    Das, J.2    Chattopadhyay, S.3
  • 32
    • 0032514516 scopus 로고    scopus 로고
    • Solid phase synthesis of substituted coumarin-3-carboxylic acids via the Knoevenagel condensation
    • Watson, B. T.; Christiansen, G. E. Solid phase synthesis of substituted coumarin-3-carboxylic acids via the Knoevenagel condensation Tetrahedron Lett. 1998, 39, 6087-6090
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6087-6090
    • Watson, B.T.1    Christiansen, G.E.2
  • 33
    • 0033411256 scopus 로고    scopus 로고
    • Solvent-free one-pot rapid synthesis of 3-carboxycoumarins
    • Bandgar, B. P.; Uppalla, L. S.; Kurule, D. U. Solvent-free one-pot rapid synthesis of 3-carboxycoumarins Green Chem. 1999, 1, 243-245
    • (1999) Green Chem. , vol.1 , pp. 243-245
    • Bandgar, B.P.1    Uppalla, L.S.2    Kurule, D.U.3
  • 34
    • 0041032836 scopus 로고    scopus 로고
    • Solvent-free synthesis of 3-carboxycoumarins
    • Scott, J. L.; Taston, C. L. Solvent-free synthesis of 3-carboxycoumarins Green Chem. 2000, 2, 245-247
    • (2000) Green Chem. , vol.2 , pp. 245-247
    • Scott, J.L.1    Taston, C.L.2
  • 35
    • 57249113661 scopus 로고    scopus 로고
    • Uncatalysed reactions in water: Part 2. Preparation of 3-carboxycoumarins
    • Maggi, R.; Bigi, F.; Carloni, S.; Mazzacani, A. Uncatalysed reactions in water: Part 2. Preparation of 3-carboxycoumarins Green Chem. 2001, 3, 173
    • (2001) Green Chem. , vol.3 , pp. 173
    • Maggi, R.1    Bigi, F.2    Carloni, S.3    Mazzacani, A.4
  • 36
    • 0344813713 scopus 로고    scopus 로고
    • Synergistic activities of antituberculosis drugs with cerulenin and trans-cinnamic acid against Mycobacterium
    • Rastogi, N.; Goh, K. S.; Horgen, L.; Barrow, W. W. Synergistic activities of antituberculosis drugs with cerulenin and trans-cinnamic acid against Mycobacterium FEMS Immunol. Med. Microbiol. 1998, 21, 149-157
    • (1998) FEMS Immunol. Med. Microbiol. , vol.21 , pp. 149-157
    • Rastogi, N.1    Goh, K.S.2    Horgen, L.3    Barrow, W.W.4
  • 37
    • 52649120277 scopus 로고    scopus 로고
    • Insulin-releasing properties of a series of cinnamic acid derivatives in vitro and in vivo
    • Adisakwattana, S.; Moonsan, P.; Yibchok-Anun, S. Insulin-releasing properties of a series of cinnamic acid derivatives in vitro and in vivo J. Agric. Food Chem. 2008, 56, 7838-7844
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 7838-7844
    • Adisakwattana, S.1    Moonsan, P.2    Yibchok-Anun, S.3
  • 38
    • 0001011682 scopus 로고    scopus 로고
    • Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds
    • Chen, J. H.; Ho, C. T. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds J. Agric. Food Chem. 1997, 45, 2374-2378
    • (1997) J. Agric. Food Chem. , vol.45 , pp. 2374-2378
    • Chen, J.H.1    Ho, C.T.2
  • 39
    • 4644257234 scopus 로고    scopus 로고
    • Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations
    • Narasimhan, B.; Belsare, D.; Pharande, D.; Mourya, V.; Dhake, A. Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations Eur. J. Med. Chem. 2004, 39, 827-834
    • (2004) Eur. J. Med. Chem. , vol.39 , pp. 827-834
    • Narasimhan, B.1    Belsare, D.2    Pharande, D.3    Mourya, V.4    Dhake, A.5
  • 40
    • 0035203337 scopus 로고    scopus 로고
    • Structure - Hepatoprotective activity relationship of 3,4-dihydroxycinnamic acid (caffeic acid) derivatives
    • Perez-Alvarez, V.; Bobadilla, R. A.; Muriel, P. Structure - hepatoprotective activity relationship of 3,4-dihydroxycinnamic acid (caffeic acid) derivatives J. Appl. Toxicol. 2001, 21, 527-531
    • (2001) J. Appl. Toxicol. , vol.21 , pp. 527-531
    • Perez-Alvarez, V.1    Bobadilla, R.A.2    Muriel, P.3
  • 41
    • 0008179954 scopus 로고
    • Structure of acacigenin-B, a novel triterpene ester isolated from Acacia concinna
    • Anjaneyulu, A. S. R.; Bapuji, M.; Rao, L. R.; Sree, A. Structure of acacigenin-B, a novel triterpene ester isolated from Acacia concinna Phytochemistry 1979, 18, 463-466
    • (1979) Phytochemistry , vol.18 , pp. 463-466
    • Anjaneyulu, A.S.R.1    Bapuji, M.2    Rao, L.R.3    Sree, A.4
  • 42
    • 0030902815 scopus 로고    scopus 로고
    • Acacia concinna saponins. I. Structures of prosapogenols, concinnosides A-F: Isolation from the alkaline hydrolysate of the highly polar saponin fraction
    • Gafur, M. A.; Obata, T.; Kiuchi, F.; Tsuda, Y. Acacia concinna saponins. I. Structures of prosapogenols, concinnosides A-F: Isolation from the alkaline hydrolysate of the highly polar saponin fraction Chem. Pharm. Bull. 1997, 45, 620-625
    • (1997) Chem. Pharm. Bull. , vol.45 , pp. 620-625
    • Gafur, M.A.1    Obata, T.2    Kiuchi, F.3    Tsuda, Y.4
  • 43
    • 0006553711 scopus 로고
    • Evaluation of surface active properties of saponins isolated from Acacia concinna dc pods
    • Pratap, G.; Bhaskar Rao, V. S. Evaluation of surface active properties of saponins isolated from Acacia concinna d.c. pods Fett Wiss. Technol. 1987, 89, 205-208
    • (1987) Fett Wiss. Technol. , vol.89 , pp. 205-208
    • Pratap, G.1    Bhaskar Rao, V.S.2
  • 44
    • 0006584516 scopus 로고
    • Saponins and sapogenins XXV: The sapogenin of Acacia concinna d.c. pods and the constitution of acacic acid
    • Varshney, I. P.; Shamsuddin, K. M. Saponins and sapogenins XXV: The sapogenin of Acacia concinna d.c. pods and the constitution of acacic acid Tetrahedron Lett. 1964, 5, 2055-2058
    • (1964) Tetrahedron Lett. , vol.5 , pp. 2055-2058
    • Varshney, I.P.1    Shamsuddin, K.M.2
  • 46
    • 81755187111 scopus 로고    scopus 로고
    • Rapid one-pot, four component synthesis of pyranopyrazoles using heteropolyacid under solvent-free condition
    • Chavan, H. V.; Babar, S, B.; Hoval, R. U.; Bandgar, B. P. Rapid one-pot, four component synthesis of pyranopyrazoles using heteropolyacid under solvent-free condition Bull. Korean Chem. Soc. 2011, 32, 3963-3966
    • (2011) Bull. Korean Chem. Soc. , vol.32 , pp. 3963-3966
    • Chavan, H.V.1    Babar, S.B.2    Hoval, R.U.3    Bandgar, B.P.4
  • 47
    • 79961072136 scopus 로고    scopus 로고
    • Polyethylene glycol in water: A simple, efficient and green protocol for the synthesis of quinoxalines
    • Chavan, H. V.; Adsul, L. K.; Bandgar, B. P. Polyethylene glycol in water: A simple, efficient and green protocol for the synthesis of quinoxalines J. Chem. Sci. 2011, 123, 477-483
    • (2011) J. Chem. Sci. , vol.123 , pp. 477-483
    • Chavan, H.V.1    Adsul, L.K.2    Bandgar, B.P.3
  • 49
    • 77954309541 scopus 로고    scopus 로고
    • Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles
    • Tandon, V. K.; Maurya, H. K. Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles Tetrahedron Lett. 2010, 51, 3843-3847
    • (2010) Tetrahedron Lett. , vol.51 , pp. 3843-3847
    • Tandon, V.K.1    Maurya, H.K.2
  • 50
    • 70549089934 scopus 로고    scopus 로고
    • Sodium stearate-catalyzed multicomponent reactions for efficient synthesis of spirooxindoles in aqueous micellar media
    • Wang, L.-M.; Jiao, N.; Qiu, J.; Yu, J.-J.; Liu, J.-Q.; Guo, F.-L.; Liu, Y. Sodium stearate-catalyzed multicomponent reactions for efficient synthesis of spirooxindoles in aqueous micellar media Tetrahedron 2010, 66, 339-343
    • (2010) Tetrahedron , vol.66 , pp. 339-343
    • Wang, L.-M.1    Jiao, N.2    Qiu, J.3    Yu, J.-J.4    Liu, J.-Q.5    Guo, F.-L.6    Liu, Y.7
  • 51
    • 34247239420 scopus 로고    scopus 로고
    • Tetrabutylammoniumbromide mediated Knoevenagel condensation in water: Synthesis of cinnamic acids
    • Gupta, M.; Wakhloo, B. P. Tetrabutylammoniumbromide mediated Knoevenagel condensation in water: Synthesis of cinnamic acids Arkivoc 2007, 94-98
    • (2007) Arkivoc , pp. 94-98
    • Gupta, M.1    Wakhloo, B.P.2
  • 52
    • 0032578889 scopus 로고    scopus 로고
    • The ultrasound promoted Knoevenagel condensation of aromatic aldehydes
    • James McNulty, J.; Steere, J. A.; Wolf, S. The ultrasound promoted Knoevenagel condensation of aromatic aldehydes Tetrahedron Lett. 1998, 39, 8013-8016
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8013-8016
    • James McNulty, J.1    Steere, J.A.2    Wolf, S.3
  • 54
    • 48749131911 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of cinnamic acid derivatives in the presence of PPE and under solvent-free condition
    • Mobinikhaledi, A.; Foroughifar, N.; Jirandehi, H. F. Microwave-assisted synthesis of cinnamic acid derivatives in the presence of PPE and under solvent-free condition Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 2008, 38, 428-430
    • (2008) Synth. React. Inorg., Met.-Org., Nano-Met. Chem. , vol.38 , pp. 428-430
    • Mobinikhaledi, A.1    Foroughifar, N.2    Jirandehi, H.F.3
  • 55
    • 0003880735 scopus 로고    scopus 로고
    • Phosphorus oxychloride in organic synthesis. Synthesis of cinnamic acid derivatives
    • Simonyan, A. V. Phosphorus oxychloride in organic synthesis. Synthesis of cinnamic acid derivatives Pharm. Chem. J. 1999, 33, 158-159
    • (1999) Pharm. Chem. J. , vol.33 , pp. 158-159
    • Simonyan, A.V.1


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